Organic polymeric materials such as plastics and resins are subject to thermal, oxidative and/or photodegradation. A great variety of stabilizers are known in the art for stabilizing a diversity of substrates. Their effectiveness varies depending upon the causes of degradation and the substrate to be stabilized. In general, it is difficult to predict which stabilizers will be most effective and most economical for any one area of stabilization. For example, stabilizer effectiveness in reducing volatility may depend upon preventing bond scission in the substrate molecule. Limiting embrittlement and retaining elasticity in a polymer or rubber may require prevention of excessive crosslinking and/or chain scission. Prevention of discoloration may require inhibiting reactions which yield new chromophores or color bodies in the substrate or stabilizer. Problems of process stability and incompatibility must also be considered.
Various organic hydroxylamine compounds are generally known and some are commerically available. A number of patents disclose nitrogen-substituted hydroxylamines as antioxidant stabilizers for various substrates including polyolefins, polyesters, polyurethanes, elastomers and poly(arylene sulfides). U.S. Pat. Nos. 3,432,578; 3,644,278; 3,778,464; 3,408,422; 3,926,909; 4,316,996; 4,386,224 and 4,782,105 are representative of such patents which basically disclose N,N-dialkyl-, N,N-diaryl- and N,N-diaralkylhydroxylamines and their stabilization effects.
In addition, various N,N,O-trisubstituted and N,O-disubstituted hydroxylamines are disclosed in the literature. For example, U.S. Pat. No. 3,184,500 describes R.sub.2 NOCH.sub.2 CH.sub.2 O-Acyl where R is lower alkyl; U.S. Pat. No. 3,344,190 describes R.sub.2 NOCH.sub.2 CH.sub.2 OH where R is lower alkyl; U.S. Pat. No. 3,869,278 describes (R).sub.2 NOR.sub.1 where R is alkyl and R.sub.1 is inter alia alkyl and phenyl, as fruit abscission agents; German No. 1,237,129 discloses the preparation of N,N,O-trisubstituted hydroxylamines by UV irradiation of amine oxides; L. A. Paquette [J. Org. Chem. 29, 3545 (1964)] describes the preparation of R.sub.2 NCH.sub.2 CH.sub.2 ONH.sub.2 where R.sub.2 N are heterocyclic groups; E. I. Schumann et al. [J. Med. Chem. 7, 329 (1964)] describe the preparation of several O-aralkylhydroxylamines useful as pharmaceutical agents; A. T. Fuller [J. Chem. Soc., 1947, 963 (pt 2)] reports the preparation of a series of O-alkyl and O-O'-alkylenehydroxylamines from hydroxyurethanes with potential antibacterial activity; Bernhart [Tetrahedron Letters, 29, 2493 (1974)] describes the preparation of a series of N,O-dialkylhydroxylamines by the reduction of O-alkylbenzaldoximes; B. V. Tronov et al, [Chem. Abst., 66, 37339f (1967)] describe the preparation and properties of N-alkoxydiethylamines; O-alkylation of N,N-diethylhydroxylamine is described by E. Flesia et al (Tetrahedron Letters, 1979, 197); I. M. Bortori et al., [Chem. Abst. 73, 55743g (1969)] describe the synthesis and antibacterial properties of N-(aryloxy)diethylamines; F. Klages [Ber., 96, 2387 (1963)] describes the preparation of N,N-dibenzyl-O-ethyl-hydroxylamine and N,N-di-tert-butyl-O-benzylhydroxylamine; and Japanese No. 69/25772 [Chem. Abst. 72, 78685h (1970)] describes the preparation (R')(OR)NCH.sub.2 CH.sub.2 CO(C.sub.6 H.sub.4 X) useful as anti-inflammatory drugs. It is noted that these various compounds are all indicated for pharmaceutical or agricultural uses.
O-Alkenyl substituted hydroxylamines are also known, but again only for pharmaceutical or agricultural uses. Representative of such references are European No. 29,171; European No. 103,895; U.S. Pat. No. 4,226,612; Japanese Sho No. 57-45143; German No. 2,541,702; German No. 2,439,104; U.S. Pat. No. 3,755,577; German No. 3,728,278 and European No. 110,280.
U.S. Pat. No. 4,626,411 teaches the use of N,N,O-trisubstituted hydroxylamines as corrosion inhibitors. The O-substitution in said compounds is given as hydrogen, lower alkyl or aryl. There is no disclosure or suggestion of O-alkenyl substitution in said compounds.
U.S. Pat. No. 4,696,964 does teach the use of N,O-disubstituted and N,N,O-trisubstituted hydroxylamines as stabilizers for a variety of substrates. There is no disclosure or suggestion in this patent that any of the groups being substituted on the hydroxylamine moiety should be alkenyl. The advantages observed with the instant compounds as stabilizers were not even comtemplated by this closest of the prior art.